There's A First Time For Everything
by Perry-Dice
Summary: Sam, Dean, and Cas discover the depth of their bond and finally act on it, but their memories reveal that the idea of a relationship like that isn't completely new to them. Wincestiel. Threesome.


When all three of them realized it, sitting in a dump of a motel somewhere between Indianapolis and Fort Wayne, the idea was not completely foreign to them.

Sam was flipping through a crumbling old book he'd stolen from the local library and trying to explain something important about stopping the apocalypse, but Dean was shouting because he was tired and restless and furious at himself for allowing the situation to unfold and Castiel could not listen to both of them at the same time so he settled for exploding the overhead light.

Standing there in the dark they all realized the predicament. But it wasn't completely insane.

Sam realized he was in love with two people at the same time.

Dean realized he was in love with a man.

Castiel realized he was in love.

Sam had been in a threesome before. It was his birthday and he had no idea how Jess had found out and hidden her plan, but she managed to surprise him with a cake. Sam had blushed and told her that it wasn't necessary, but secretly he was elated. Sitting there with a beautiful girlfriend and an honest to god birthday cake, he felt both incredibly normal and incredibly lucky.

When Sam suggested that he go get some work done for a class, Jess' face fell.

"What? I thought you had that friend of yours from high school coming up this weekend? Won't you guys wanna catch up?" He said, stroking his fingers down her soft cheek. Jess looked at the floor, but her lips were curling into her familiar mischievous smirk.

"She wanted to meet you Sam! Come on, she's my best friend, I know you'll love her." Jess pleaded, eyes sparkling with laughter. "At least come with me to meet her."

Jess' friend turned out to be a very small woman with short dark hair and a wide grin named Natalie. Sam found out over a few beers in Jess' dorm room that Natalie went to UCLA, studied film, and believed that any one who still refused to read Harry Potter was not worth knowing. It was at that point that Sam began to feel extremely uncomfortable, as he abruptly realized that even with Jess standing right next to him, he was extremely attracted to her best friend.

Love, for Sam, was not something he could hold back. He craved more, from everyone. Not just sex, Sam wanted connection. Not that he wasn't committed to Jess, he cherished every moment with her, but Sam wanted to have moments with Jess that might include Natalie.

In the midst of his raging internal conflict against the social constructs imposed upon him by a cruel, unforgiving society, Sam barely noticed the way the three of them were sinking onto Jess' tiny dorm room bed, forced to squeeze tightly against each other.

Around eleven all three of them were fairly drunk and laughing fairly hard. Sam was pressed between the wall and the bed with Jess snuggled against him as Natalie wrapped herself around Jess to keep from sliding off the bed. As Sam shifted his weight slightly, Natalie nearly went over the edge, and when Sam and Jess both grabbed for her, they ended up tumbling into a heap on the ground.

For an impossibly long moment, they all stared wide-eyed at one another, too close and too entangled for friendly intimacy.

"Do you want to…?" Jess courageously voiced her thoughts, breath tickling against Sam's ear.

"Please." Sam and Natalie groaned in unison.

At first, their attempts were more awkward than Sam's early teenaged fumblings with a girl who turned out to be a brain-sucking monster. However, they eventually settled into a sort of rhythm.

Jess straddled Sam and her familiarity comforted his jangled nerves. Sam held firmly onto Natalie's thighs as he concentrated his mouth on the space between them. He could hear Jess give a little gasping cry as she wrapped her arms around Natalie's waist. Natalie gave a husky moan that sent a wave of heat shivering down to Sam's cock. He could feel Natalie quivering above him, her hands running through his hair, and he could feel Jess running her fingernails gently down his stomach as she moved with increasing intensity on top of him.

Sam was beginning to come apart, losing concentration and resorting to sloppy tongue movements on Natalie. His entire lower body felt white hot, every movement sending him closer. Natalie loses it before he does, shaking and letting out a long gasp. She slides off of him and moves to nuzzle her way down Jess' neck.

Sam and Jess go together, as usual.

The next morning, they all have to sneak down to the shower, laughing hysterically as people in the hall cast quizzical glances at them. Natalie vows to come back and see them again, but things come up.

By that time next year, Jess is dead, and Sam no longer cares about the plans he made before.

Dean has been with a man before. He was sixteen years old and John had dropped them off in some middle of nowhere town in Iowa. Sam had been begging to finish the school year properly, so John drove off vowing to give them two months to finish the year and drop by when he could.

Dean was furious at first. He was old enough to be taken on major hunts, had been on a few that year, but spending a month languishing in the countryside was as far removed from training as he'd ever been.

His perspective changed when he and Sam started school. Generally, it was Sam who actually made friends. There were always a couple of stragglers, shy and unsure, who shuffled up to say goodbye before they drove away. Dean, while giving off every appearance of being extremely well liked, left behind a string of angry ex-girlfriends and a few scumbags with connections who dealt in less than legal substances.

But when Dean slumped into a desk on his first day, the captain of the baseball team introduced himself as Tyler and Dean suddenly had a group of friends. They didn't really talk about anything important, mainly cars and athletic prospects and which girls had the best tits, but Dean enjoyed the company. Outside of school, they never asked to see his house or meet his parents; they all just piled into Tyler's van and drank vodka out of a water bottle behind the gas station.

Tyler was the closest Dean had ever come to a real friend. He mainly talked about baseball and Dean barely talked at all, but he started watching. He noticed the breadth of Tyler's shoulders, the flash of white teeth against smooth dark skin, the movement of muscle under a thin shirt.

John's visits became scarcer. He picked up Dean for a run of the mill salt and burn then didn't call for weeks. Dean told him over the phone that he was actually pulling a 3.5 GPA for the first time in his life and John just grunted and asked if he could put together a few dozen salt rounds before the weekend.

Sam finished the year with all A's and Dean felt almost sorry that they wouldn't be back in the fall.

On their last day in town, Dean found himself sliding into Tyler's van one last time. They went to his house and Dean picked the lock on the liquor cabinet. Dean had so many fake IDs at that point that he was verging on mild alcoholism, but Tyler's parents had expensive whiskey so Dean drank up.

After nearly half a bottle, Dean lay on the couch, head spinning. He said something incoherent and then laughed to himself for a few minutes. Tyler was no better, propping himself against the arm of the couch, but eventually losing his grip and sliding onto Dean.

Tension hung in the air for a long moment and Dean waited breathlessly for Tyler to shake it off and pull himself up. But Tyler moved upward and placed his lips next to Dean's ear.

"I've wanted you since you swaggered your way out of that damn car." He breathed and trailed his mouth over to Dean's.

At first, Dean rationalized that he was too drunk to be alarmed or protesting. But the enthusiasm he responded with belied that claim. Sloppy and urgent, Tyler yanked his shirt off then moved on to Dean.

When Tyler unzipped his pants and guided Dean's hand down, Dean rationalized that he was simply helping a friend in need. He'd done it to himself a thousand times, why should giving another guy a hand be any different? Dean's practiced strokes did their work on Tyler, but even as he wiped himself off with his discarded shirt, he refused to let Dean squirm away.

When Tyler undid his belt, Dean thought he should protest. He knew he should leave, or maybe just kick the crap out of Tyler for trying to force him into something like this. But for some reason the only thing he could get out of his idiotic mouth was,

"Please. Please."

An unfamiliar hand slipped his cock into the open air. Dean lay his head back against the couch and breathed deeply. He felt Tyler's lips teasing lightly at the tip, unbearably soft. Then the warmth of a mouth, the devastating flick of a tongue, and the sucking pressure sent every thought out of his mind.

He tried to surpass the gasps and growling moans, fought to stop his hips from bucking upwards. Tyler abruptly pulled his mouth away and looked at Dean with a surprisingly hard stare.

"You're leaving tomorrow, right? And you won't tell a soul?"

"Yes, the secrets safe or whatever, would you please just-" Dean panted, desperate and shaking.

"So impatient. Enjoy your goodbye present." Tyler grinned, drawing his words out agonizingly slowly. Dean gave a little yelp when Tyler returned swiftly to his enthusiastic work, hands stroking up Dean's thighs. Dean came with a long hiss through his teeth and a clench of his fingers.

By the time he was completely sober, head resting against the cold glass of the impala's window as they sped through the night, Dean had already vowed to keep his promise and never tell a soul.

When he drops out of high school he wonders what good it ever did anyone.

Castiel called Dean while standing quietly deep in an Arkansas pine forest. For days he had been searching land and sea, combing through the sands, clutching the amulet and willing it to flare with heat. After no success, he called Dean to ask where he was.

"I'm at a motel, uh, the Thunderbird motel outside of the twin cities." Dean whispered, voice strangely hurried. "Could you give me a few hours?"

"I'll be brief." Castiel rumbled. "You can sleep later."

"Cas… I'm with a girl okay? Just give me little bit." Dean spit out irritably and hung up.

Castiel snapped the phone shut and considered dashing it against the ground. Then he turned on his heel and vanished into the darkness. He reappeared abruptly in an empty room of the Thunderbird motel then sat solemnly on the bed to wait.

He waited ten minutes, completely still. But silence gave Castiel time to reflect. As he perched on the bed, he realized he was tired. The muscles of his vessel ached from overexertion and his eyes felt heavy. Castiel hung his head, feeling wretchedly human.

A noise interrupted his reverie. Muffled through the wall, Castiel distinctly heard Dean talking. Perhaps it was his still enhanced angelic hearing or perhaps it was the cheapness of that particular motel, but Castiel could make out definitively the sound of Dean speaking softly and a soft fluty voice responding.

A creeping feeling that he should leave and avoid hearing what came next overtook Castiel, but a reckless desire kept him rooted to the spot. In another moment, Castiel heard the girl laugh and Dean make a low sound almost like a growl. Castiel shivered.

In a moment, Castiel perceived his increased humanity in the form of heat curling in his groin. He gasped a little at the feeling of himself pressed against the suit pants. A snap judgment sent him reaching for his zipper. Castiel had watched humanity for centuries; he knew how men dealt with this feeling.

Despite understanding the motions, Castiel had no idea of the sensations that went along with them. His first touch was light and cautious like a foal's first step. Gradually he moved more firmly, stroking himself faster and faster. He threw back his head, his unoccupied hand clutching at his coat. A guttural sound escaped from his throat and he spread his legs wider, urgency and heat flooding his body. His hips rocked forward desperately.

Through the wall, Castiel heard the girl moan and Dean give a choked shout. The sound sent him over the edge and Castiel bit his lip until he bled as his first orgasm rushed over him.

After a breathless moment, Castiel opened his eyes and stared around the empty room, panic beginning to overcome him. He did not understand the very human emotions, the endorphins, the sick sense of shame. He still had enough grace to leave the room clean and untouched, and when Dean called in the morning to ask why he never showed, Castiel lied easily that he'd been busy.

Lies were another new thing he was learning. The other was called jealousy.

Back in the dark motel room somewhere in Indiana Castiel stands between Sam and Dean, frustrated and scared.

He looks over to Sam. Sam understands Castiel. They get along simply, concentrating on work, research, and solving problems. Sam is never judgmental on account of his previous mistakes, and he accepts Castiel's tendency to think only of the greater good. They can love easily.

Then Castiel glances at Dean. His relationship with Dean is difficult. Dean calls him out on everything, acts infuriatingly insensitive towards everyone, ignores Castiel then expects everything from him, and Castiel loves him and wouldn't want it any other way. They fight, but it only makes them stronger.

The motel room is dimly lit from the light of the window as the three of them stand, shell-shocked, for another long moment. Then Castiel strides purposefully over to Sam and before Sam can get out more than a muffled cry of shock, Castiel kisses him. His lips are soft and part readily as they move together with perfect balance.

Castiel pulls away when he hears Dean get up and make for the door, mumbling about getting out of their way if they're going to start that. Castiel catches him by the arm and spins him around. Heartbreak is etched across Dean's smile as he congratulates the pair. Castiel kisses him as well. Dean fights it at first, but Castiel presses forward until Dean submits and they clash together with such intensity that Castiel nearly bites his own tongue off.

"What the hell are we doing?" Dean laughs nervously as they break apart with a gasp.

"Sitting down." Castiel says blandly as he yanks both Winchesters onto the bed. He brushes Sam's lips. He bites Dean a little. Then Castiel slowly pushes both of them inward and they run their mouths down Castiel's neck.

Abruptly and with every semblance of true guile, Castiel jerks backwards. Sam lurches forwards into a reeling Dean and somewhere in the middle their mouths just meet and stay connected for far too long.

The three stare at each other again. Perhaps they were not as prepared for the moment as they had thought.

"I just… kissed a man." Sam splutters.

"I just kissed my brother." Dean chokes out with dull horror.

"I just kissed a human!" Castiel groans and flops backwards onto the pillows.

The next morning they spend sprawled together in the too small bed. Sam observes,

"The ones who save the world are never exactly normal, I guess."


End file.
